| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348136 | Tetrahedron: Asymmetry | 2007 | 11 Pages |
Nucleophilic addition reactions of 2-lithiated N-phenylsulfonylindoles with (R)-N-tert-butanesulfinyl aldimines provided chiral (2-indolyl) methanamine derivatives in moderate to good yields (up to 100%) with excellent diastereoselectivities (>99:1), in which no additional Lewis acids were required.
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(R,E)-2-Methyl-N-(4-nitrobenzylidene)propane-2-sulfinamideC11H14N2O3S[α]D20=-58.0 (c 2.5, CHCl3)
(R,E)-N-(2-Chlorobenzylidene)-2-methylpropane-2-sulfinamideC11H14NOSCl[α]D20=-195.6 (c 4.3, CHCl3)
(R,E)-N-(2-Bromobenzylidene)-2-methylpropane-2-sulfinamideC11H14NOSBr[α]D20=-207.2 (c 3.1, CHCl3)
(R,E)-N-(2-Methoxybenzylidene)-2-methylpropane-2-sulfinamideC12H17NO2S[α]D20=-230.4 (c 1.9, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(iso-propanyl)methane]-2-tert-butanesulfinamideC22H28N2O3S2Dr >99:1[α]D20=+145.3 (c 1.8, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(tert-butyl)methane]-2-tert-butanesulfinamideC23H30N2O3S2Dr >99:1[α]D20=+211.2 (c 2.9, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)phenylmethane]-2-tert-butanesulfinamideC25H26N2O3S2Dr>99:1[α]D20=+38.0 (c 2.0, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-chlorophenyl)methane]-2-tert-butanesulfinamideC25H25N2O3S2ClDr >99:1[α]D20=+46.7 (c 0.6, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-nitrophenyl)methane]-2-tert-butanesulfinamideC25H25N5O3S2Dr >99:1[α]D20=+67.7 (c 2.7, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(o-chlorophenyl)methane]-2-tert-butanesulfinamideC25H25N2O3S2Dr >99:1[α]D20=+23.4 (c 1.0, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(o-bromophenyl)methane]-2-tert-butanesulfinamideC25H25BrN2O3S2Dr >99:1[α]D20=+38.3 (c 2.2, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-methylphenyl)methane]-2-tert-butanesulfinamideC26H28N2O3S2Dr >99:1[α]D20=+54.9 (c 2.6, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-methoxyphenyl)methane]-2-tert-butanesulfinamideC26H28N2O4S2Dr>99:1[α]D20=+51.9 (c 1.1, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(o-methoxyphenyl)methane]-2-tert-butanesulfinamideC26H28N2O4S2Dr >99:1[α]D20=-20.9 (c 2.8, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)naphthylmethane]-2-tert-butanesulfinamideC29H28N2O3S2Dr >99:1[α]D20=+17.1 (c 1.2, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(9-anthryl)methane]-2-tert-butanesulfinamideC33H30N2O3S2Dr >99:1[α]D20=-69.3 (c 1.0, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(fur-2-yl)methane]-2-tert-butanesulfinamideC23H24N2O4S2Dr >99:1[α]D20=-16.0 (c 0.9, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)styrylmethane]-2-tert-butanesulfinamideC27H28N2O3S2Dr >99:1[α]D20=+6.5 (c 2.2, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)benzylmethane]-2-tert-butanesulfinamideC26H28N2O3S2Dr>99:1[α]D20=+4.4 (c 0.2, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-3-methyl-indol-2-yl)(p-chlorophenyl)methane]-2-tert-butanesulfinamideC26H27N2O3S2ClDr >99:1[α]D20=+93.7 (c 0.8, CHCl3)
(RS,S)-N-[(1-Phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methane]-2-tert-butanesulfinamideC25H24N3O5S2ClDr >99:1[α]D20=+144.6 (c 2.0, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-2-yl)(iso-propanyl)methane]-tert-butanesulfonamideC22H28N2O4S2Ee = 99%[α]D20=+42.9 (c 0.9, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-indole-2-yl)(tert-butyl)methane]-tert-butanesulfonamideC23H30N2O4S2Ee >99%[α]D20=+134.7 (c 1.5, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-chlorophenyl)methane]-p-toluenesulfonamideC28H23N2O4S2ClEe >99%[α]D20=+122.7 (c 1.5, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-nitrophenyl)methane]-p-toluenesulfonamideC28H23N3O6S2Ee = 99%[α]D20=+103.2 (c 2.8, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(o-bromophenyl)methyl]-p-toluenesulfonamideC28H23N2O4S2BrEe >99%[α]D20=+52.6 (c 2.3, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(p-methoxyphenyl)methane]-p-toluenesulfonamideC29H26N2O5S2Ee = 99%[α]D20=+78.6 (c 2.0, CHCl3)
(R)-N-[(1-Phenylsulfonyl-1H-indol-2-yl)(2-furyl)methyane]-p-toluenesulfonamideC26H22N2O5S2Ee = 98%[α]D20=+64.6 (c 1.3, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-3-methyl-indol-2-yl)(p-chlorophenyl)methane]-p-toluenesulfonamideC29H25ClN2O4S2Ee = 98%[α]D20=+117.5 (c 0.6, CHCl3)
(S)-N-[(1-Phenylsulfonyl-1H-4-nitro-indol-2-yl)(p-chlorophenyl)methane]-p-toluenesulfonamideC28H22ClN3O6S2Ee = 98%[α]D20=+77.8 (c 0.7, CHCl3)
(S)-N-[(1H-Indol-2-yl)(p-chlorophenyl)methyl]-p-toluenesulfonamideC22H19N2O2SClEe = 97%[α]D20=-24.3 (c 2.8, CH2Cl2)
